I’m an avid people-watcher and there’s no better place to see some interesting characters than on the subways in NYC, especially during one’s commute. Unfortunately, I tend to be pretty shy, so even when I see people who I’m sure would be awesome friends, I never strike up a conversation. Here are my love letters to the coulda-woulda-shoulda friendships on the 4, 5 and 6 trains. Consider this The Jane Dough‘s platonic equivalent of Craigslist’s “Missed Connections” page.

The woman holding the giant goldfish bowl, trying to maneuver her way through the revolving bar at Grand Central during rush hour without spilling her precious cargo. I wish I had struck up a conversation with her because someone who understands the importance of taking your fish out for some fresh, subway air every once in a while seems like the kind of person who has her priorities in order.

The woman holding the “You’re Special!” balloon at Union Square. This is the most perfect balloon in the entire world. Its everything you could ever want it to be because it’s so generic and could apply to virtually any situation — birthday, graduation, anniversary, new baby, promotion, a cynical performance art piece, etc. If she was on her way to give the balloon to someone else, I hope she’s the kind of practical lady who has a bunch of “You’re Special!” balloons in her apartment for any occasion that might arise. And if she was the receiver, and if she’s really as special as she alleges, then I really should have tried to be her friend.

The woman who dressed her probably 7-year-old daughter in this shirt. “Gangsta rap made me do it,” the shirt read matter-of-factly. I have absolutely no idea what that is supposed to mean but anyone who has the smarts to realize that a woman’s crop top makes a perfectly acceptable full-length shirt for a child is probably someone I would want in my wedding party.

The older woman wearing this badass fox skirt from Anthropologie and the highest gold heels I’ve ever seen. I had never realized that my wardrobe was so severely lacking in woodland creatures before I saw her. I don’t know what it was about her but she seemed like the kind of person who would have an animal statement piece in each of her outfits, so I would have loved to become her friends so we could swap closets for a while.

The really tall woman wearing a multi-colored maxi-dress. This was probably the closest I got to actually talking to someone: I am also a really tall woman so I’m always searching for tall female friends to add to my social circle and I too was wearing a maxi-dress at the time. Was it fate? Kismet? I felt like we had a palpable twin connection as we waited on the subway platform next to each other, nonchalantly glancing at one another every so often to see if the other had noticed this incredible phenomenon of long women wearing long dresses. I wish I had befriended her so we could talk about tall lady problems, namely how hard it is to find a cute maxi-dress that’s long enough to cover Amazonian legs.